Users susceptible to man-in-the-middle attacks due to corporate https inspection

A large number of companies use “security” products to inspect HTTPS traffic for detecting malware and prevent other types of attacks. However, they might inadvertently make their user’s more susceptible to man-in-the-middle attacks by  decrypting and re-encrypting HTTPS connections.

The U.S. Computer Emergency Readiness Team (US-CERT) warns in an advisory that HTTPS inspection products don’t mirror the security attributes of the original HTTPS connections between the client and the server (Mirror: HTTPS Interception Weakens TLS Security | US-CERT).

HTTPS inspection is deployed in companies for checking the encrypted traffic coming from an HTTPS website to make sure it does not contain any malware or any other type of attacks. It basically performs a decryption and re-encryption of the client’s connection to an HTTPS server. The “security” products (proxy, web-gateway, firewall etc.) establish the connection on the client’s behalf by first decrypting the client’s HTTPS connection and re-encrypting the traffic sent to the HTTPS server. The client is served with a different, locally generated certificate by the security product which essentially perform a man-in-the-middle attack.

In some enterprise environments, an HTTPS connection may even be intercepted and re-encrypted multiple times. For example, at the network perimeter by a security gateway product and later, on the endpoint by a client’s antivirus program which needs to inspect the traffic for malware.

The problem revolves around the fact that the client’s browser no longer validates the real certificate issued by the server because its replaced with a locally generated certificate from the security product. In return, the task of validating the certificate now falls to the intercepting proxy.

According to the published advisory, those security products are evidently pretty bad at validating server certificates. An investigation conducted by researches from Google, Mozilla, Cloudfare, and multiple Universities states that the intercepted connections use weaker cryptographic algorithms (Source: interception-ndss17). The security products even advertise support for known-broken encryption ciphers that would allow an active man-in-the-middle attack by intercepting and downgrading a connection in order to decrypt it.

The analysis by the researches found that at least 32 percent of connections to e-comerce sites and 54 percent of Cloudflare HTTPS connections, which were intercepted, became less secure than they would have been if the user had connected directly to the server.

Browser makers had a long time to properly unterstand the quirks of TLS connections and certificate validation. Therefore, there is no better client-side implementation of TLS, the protocol used for encrypting HTTPS connection, than the one found in modern browsers.
In comparison, security product vendors use outdated, customised TLS libraries where they even back-port new protocol features. Re-implementing those features found in newer libraries makes them susceptible to serious vulnerabilities.

Furthermore, the US-CERT points out another widespread problem that many products intercepting HTTPS don’t properly validate the certificate chain presented by servers. Certificate-chain verification errors are infrequently forwarded to the client, leading the client to believe that operations were performed with the correct server.

The BadSSL website allows organisations and even employees to check if their HTTPS inspection products improperly validate certificates or allow for insecure ciphers. The client test from Qualys SSL Labs also provides checks for some known TLS vulnerabitiles and weakenesses.